Phosphorus aziridine ring

Suitable methods for linking a phosphorus—nitrogen bond to the aziridine ring are the aminolysis of halogenated phosphorus compounds (2,280—282), the transamination of phosphoramines with excess aziridine (283), the reaction with phosphites (284) and phosphoramidites (285) which have a free OH group, or the reaction of phosphines with aziridines and carbon tetrachloride (286). 

The biological activity and the reactivity of aziridines vary considerably with the number and properties of the ring substituents. This paper describes the synthesis and biological activity of some sulfur-containing aziridines which are somewhat similar to phosphorus-containing chemosterilants tepa and metepa. 

Diels-Alder reactions of enantiomerically enriched 2H-azirine 3-phosphon-ates (281), a new class of chiral iminodienophiles, and dienes stereoselectively furnish optically pure, bicyclic aziridine adducts (282). Hydrogenation of (282) results in a ring opening that affords the first examples of optically pure quaternary piperidine phosphonates. Two step synthesis of an enantiomeric pure cyclic phosphite (283) and its application as a chiral phosphorus nucleophile in the asymmetric Michael addition to nitroalkenes (284) provides an efficient... 

It is striking to compare the relative novelty of these phosphorus-carbon three-membered rings with the well-established history of aziridines dating back to 1888. However, since 1963, progress has been extremely fast, in part due to the powerful 31P NMR tool, and the overall shape of the field is now definitively established. The last comprehensive review concerning these rings was published in 1990 <90CRV997> and is often referred to in this chapter. 

Rings containing Nitrogen. - The reactions of aziridines with alkylidene-phosphoranes and with phosphorus(III) nucleophiles and the reactions of... 

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